Dimethyl Sulfoxide → HCID 86619942, compound

HRID 1716324Notes

Reaction equation

HRID 1716324 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:22]2[CH2:28][CH2:27][CH2:26][CH2:25][N:24]([O:29][C:30]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:23]2=[O:49])(=[O:21])=[O:20])=[CH:15][CH:14]=1>ClCCl>[O:49]=[C:23]1[CH:22]([S:19]([C:16]2[CH:15]=[CH:14][C:13]([CH:12]=[O:11])=[CH:18][CH:17]=2)(=[O:21])=[O:20])[CH2:28][CH2:27][CH2:26][CH2:25][N:24]1[O:29][C:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 68515715HCID 68515715, compound

Product 1

HCID 86619942HCID 86619942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (0.12 ml, 2.0 M in dichloromethane) in dichloromethane (5.0 ml) was added DMSO (0.05 ml) at −78 degree C. dropwise. The mixture was stirred for 15 minutes, at which time, 3-(4-hydroxymethyl-benzenesulfonyl)-1-trityloxy-azepan-2-one (60.5 mg in 2 ml of dichloromethane) from step F was added dropwise. The resulting solution was stirred for 30 minutes and then TEA (0.9 ml) was added in one portion. The reaction mixture was stirred and warmed to 0 degree C. for a period of 15 minutes, at which time, the reaction mixture was diluted with dichloromethane and washed sequentially with water and saturated NaCl solution. The organic phase was then dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a crude material, which was then purified by a column chromatography (0˜30% EtOAc in hexane). MS: 562.1 (M+Na)+.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred
  3. temperaturewarmed to 0 degree C
  4. waitfor a period of 15 minutes
  5. washwashed sequentially with water and saturated NaCl solution
  6. dry with materialThe organic phase was then dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6db0840fd9d24810b58287ef3e0a80b9
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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